diff --git a/site/src/modules/dashboard/Navbar/DeploymentDropdown.tsx b/site/src/modules/dashboard/Navbar/DeploymentDropdown.tsx
new file mode 100644
index 0000000000000..23f0355ad3e9a
--- /dev/null
+++ b/site/src/modules/dashboard/Navbar/DeploymentDropdown.tsx
@@ -0,0 +1,151 @@
+import { css, type Interpolation, type Theme, useTheme } from "@emotion/react";
+import Button from "@mui/material/Button";
+import MenuItem from "@mui/material/MenuItem";
+import type { FC } from "react";
+import { NavLink } from "react-router-dom";
+import { DropdownArrow } from "components/DropdownArrow/DropdownArrow";
+import {
+  Popover,
+  PopoverContent,
+  PopoverTrigger,
+  usePopover,
+} from "components/Popover/Popover";
+import { USERS_LINK } from "modules/navigation";
+
+interface DeploymentDropdownProps {
+  canViewAuditLog: boolean;
+  canViewDeployment: boolean;
+  canViewAllUsers: boolean;
+  canViewHealth: boolean;
+}
+
+export const DeploymentDropdown: FC<DeploymentDropdownProps> = ({
+  canViewAuditLog,
+  canViewDeployment,
+  canViewAllUsers,
+  canViewHealth,
+}) => {
+  const theme = useTheme();
+
+  if (
+    !canViewAuditLog &&
+    !canViewDeployment &&
+    !canViewAllUsers &&
+    !canViewHealth
+  ) {
+    return null;
+  }
+
+  return (
+    <Popover>
+      <PopoverTrigger>
+        <Button
+          size="small"
+          endIcon={
+            <DropdownArrow
+              color={theme.experimental.l2.fill.solid}
+              close={false}
+              margin={false}
+            />
+          }
+        >
+          Deployment
+        </Button>
+      </PopoverTrigger>
+
+      <PopoverContent
+        horizontal="right"
+        css={{
+          ".MuiPaper-root": {
+            minWidth: "auto",
+            width: 180,
+            boxShadow: theme.shadows[6],
+          },
+        }}
+      >
+        <DeploymentDropdownContent
+          canViewAuditLog={canViewAuditLog}
+          canViewDeployment={canViewDeployment}
+          canViewAllUsers={canViewAllUsers}
+          canViewHealth={canViewHealth}
+        />
+      </PopoverContent>
+    </Popover>
+  );
+};
+
+const DeploymentDropdownContent: FC<DeploymentDropdownProps> = ({
+  canViewAuditLog,
+  canViewDeployment,
+  canViewAllUsers,
+  canViewHealth,
+}) => {
+  const popover = usePopover();
+
+  const onPopoverClose = () => popover.setIsOpen(false);
+
+  return (
+    <nav>
+      {canViewDeployment && (
+        <MenuItem
+          component={NavLink}
+          to="/deployment/general"
+          css={styles.menuItem}
+          onClick={onPopoverClose}
+        >
+          Settings
+        </MenuItem>
+      )}
+      {canViewAllUsers && (
+        <MenuItem
+          component={NavLink}
+          to={USERS_LINK}
+          css={styles.menuItem}
+          onClick={onPopoverClose}
+        >
+          Users
+        </MenuItem>
+      )}
+      {canViewAuditLog && (
+        <MenuItem
+          component={NavLink}
+          to="/audit"
+          css={styles.menuItem}
+          onClick={onPopoverClose}
+        >
+          Auditing
+        </MenuItem>
+      )}
+      {canViewHealth && (
+        <MenuItem
+          component={NavLink}
+          to="/health"
+          css={styles.menuItem}
+          onClick={onPopoverClose}
+        >
+          Healthcheck
+        </MenuItem>
+      )}
+    </nav>
+  );
+};
+
+const styles = {
+  menuItem: (theme) => css`
+    text-decoration: none;
+    color: inherit;
+    gap: 20px;
+    padding: 8px 20px;
+    font-size: 14px;
+
+    &:hover {
+      background-color: ${theme.palette.action.hover};
+      transition: background-color 0.3s ease;
+    }
+  `,
+  menuItemIcon: (theme) => ({
+    color: theme.palette.text.secondary,
+    width: 20,
+    height: 20,
+  }),
+} satisfies Record<string, Interpolation<Theme>>;
diff --git a/site/src/modules/dashboard/Navbar/Navbar.test.tsx b/site/src/modules/dashboard/Navbar/Navbar.test.tsx
index 681af84728851..93953530c2357 100644
--- a/site/src/modules/dashboard/Navbar/Navbar.test.tsx
+++ b/site/src/modules/dashboard/Navbar/Navbar.test.tsx
@@ -1,4 +1,5 @@
 import { render, screen, waitFor } from "@testing-library/react";
+import userEvent from "@testing-library/user-event";
 import { HttpResponse, http } from "msw";
 import { App } from "App";
 import {
@@ -21,6 +22,8 @@ describe("Navbar", () => {
       }),
     );
     render(<App />);
+    const deploymentMenu = await screen.findByText("Deployment");
+    await userEvent.click(deploymentMenu);
     await waitFor(
       () => {
         const link = screen.getByText(Language.audit);
@@ -34,6 +37,8 @@ describe("Navbar", () => {
     // by default, user is an Admin with permission to see the audit log,
     // but is unlicensed so not entitled to see the audit log
     render(<App />);
+    const deploymentMenu = await screen.findByText("Deployment");
+    await userEvent.click(deploymentMenu);
     await waitFor(
       () => {
         const link = screen.queryByText(Language.audit);
@@ -59,7 +64,7 @@ describe("Navbar", () => {
     render(<App />);
     await waitFor(
       () => {
-        const link = screen.queryByText(Language.audit);
+        const link = screen.queryByText("Deployment");
         expect(link).toBe(null);
       },
       { timeout: 2000 },
diff --git a/site/src/modules/dashboard/Navbar/NavbarView.stories.tsx b/site/src/modules/dashboard/Navbar/NavbarView.stories.tsx
index 2490234bd36e1..146a66b9372e3 100644
--- a/site/src/modules/dashboard/Navbar/NavbarView.stories.tsx
+++ b/site/src/modules/dashboard/Navbar/NavbarView.stories.tsx
@@ -10,6 +10,10 @@ const meta: Meta<typeof NavbarView> = {
   component: NavbarView,
   args: {
     user: MockUser,
+    canViewAuditLog: true,
+    canViewDeployment: true,
+    canViewAllUsers: true,
+    canViewHealth: true,
   },
   decorators: [withDashboardProvider],
 };
@@ -25,6 +29,7 @@ export const ForMember: Story = {
     canViewAuditLog: false,
     canViewDeployment: false,
     canViewAllUsers: false,
+    canViewHealth: false,
   },
 };
 
diff --git a/site/src/modules/dashboard/Navbar/NavbarView.test.tsx b/site/src/modules/dashboard/Navbar/NavbarView.test.tsx
index c881fa300000d..a6541ea688486 100644
--- a/site/src/modules/dashboard/Navbar/NavbarView.test.tsx
+++ b/site/src/modules/dashboard/Navbar/NavbarView.test.tsx
@@ -1,4 +1,5 @@
 import { screen } from "@testing-library/react";
+import userEvent from "@testing-library/user-event";
 import type { ProxyContextValue } from "contexts/ProxyContext";
 import { MockPrimaryWorkspaceProxy, MockUser } from "testHelpers/entities";
 import { renderWithAuth } from "testHelpers/renderHelpers";
@@ -65,6 +66,8 @@ describe("NavbarView", () => {
         canViewHealth
       />,
     );
+    const deploymentMenu = await screen.findByText("Deployment");
+    await userEvent.click(deploymentMenu);
     const userLink = await screen.findByText(navLanguage.users);
     expect((userLink as HTMLAnchorElement).href).toContain("/users");
   });
@@ -81,6 +84,8 @@ describe("NavbarView", () => {
         canViewHealth
       />,
     );
+    const deploymentMenu = await screen.findByText("Deployment");
+    await userEvent.click(deploymentMenu);
     const auditLink = await screen.findByText(navLanguage.audit);
     expect((auditLink as HTMLAnchorElement).href).toContain("/audit");
   });
@@ -97,8 +102,12 @@ describe("NavbarView", () => {
         canViewHealth
       />,
     );
-    const auditLink = await screen.findByText(navLanguage.deployment);
-    expect((auditLink as HTMLAnchorElement).href).toContain(
+    const deploymentMenu = await screen.findByText("Deployment");
+    await userEvent.click(deploymentMenu);
+    const deploymentSettingsLink = await screen.findByText(
+      navLanguage.deployment,
+    );
+    expect((deploymentSettingsLink as HTMLAnchorElement).href).toContain(
       "/deployment/general",
     );
   });
diff --git a/site/src/modules/dashboard/Navbar/NavbarView.tsx b/site/src/modules/dashboard/Navbar/NavbarView.tsx
index 440bdd44f249d..376273c8d75ee 100644
--- a/site/src/modules/dashboard/Navbar/NavbarView.tsx
+++ b/site/src/modules/dashboard/Navbar/NavbarView.tsx
@@ -9,7 +9,7 @@ import Menu from "@mui/material/Menu";
 import MenuItem from "@mui/material/MenuItem";
 import Skeleton from "@mui/material/Skeleton";
 import { visuallyHidden } from "@mui/utils";
-import { type FC, type ReactNode, useRef, useState } from "react";
+import { type FC, useRef, useState } from "react";
 import { NavLink, useLocation, useNavigate } from "react-router-dom";
 import type * as TypesGen from "api/typesGenerated";
 import { Abbr } from "components/Abbr/Abbr";
@@ -20,12 +20,9 @@ import { Latency } from "components/Latency/Latency";
 import { useAuthenticated } from "contexts/auth/RequireAuth";
 import type { ProxyContextValue } from "contexts/ProxyContext";
 import { BUTTON_SM_HEIGHT, navHeight } from "theme/constants";
+import { DeploymentDropdown } from "./DeploymentDropdown";
 import { UserDropdown } from "./UserDropdown/UserDropdown";
 
-export const USERS_LINK = `/users?filter=${encodeURIComponent(
-  "status:active",
-)}`;
-
 export interface NavbarViewProps {
   logo_url?: string;
   user?: TypesGen.User;
@@ -43,26 +40,15 @@ export const Language = {
   workspaces: "Workspaces",
   templates: "Templates",
   users: "Users",
-  audit: "Audit",
-  deployment: "Deployment",
+  audit: "Auditing",
+  deployment: "Settings",
 };
 
 interface NavItemsProps {
-  children?: ReactNode;
   className?: string;
-  canViewAuditLog: boolean;
-  canViewDeployment: boolean;
-  canViewAllUsers: boolean;
-  canViewHealth: boolean;
 }
 
-const NavItems: FC<NavItemsProps> = ({
-  className,
-  canViewAuditLog,
-  canViewDeployment,
-  canViewAllUsers,
-  canViewHealth,
-}) => {
+const NavItems: FC<NavItemsProps> = ({ className }) => {
   const location = useLocation();
   const theme = useTheme();
 
@@ -83,26 +69,6 @@ const NavItems: FC<NavItemsProps> = ({
       <NavLink css={styles.link} to="/templates">
         {Language.templates}
       </NavLink>
-      {canViewAllUsers && (
-        <NavLink css={styles.link} to={USERS_LINK}>
-          {Language.users}
-        </NavLink>
-      )}
-      {canViewAuditLog && (
-        <NavLink css={styles.link} to="/audit">
-          {Language.audit}
-        </NavLink>
-      )}
-      {canViewDeployment && (
-        <NavLink css={styles.link} to="/deployment/general">
-          {Language.deployment}
-        </NavLink>
-      )}
-      {canViewHealth && (
-        <NavLink css={styles.link} to="/health">
-          Health
-        </NavLink>
-      )}
     </nav>
   );
 };
@@ -157,12 +123,7 @@ export const NavbarView: FC<NavbarViewProps> = ({
                 )}
               </div>
             </div>
-            <NavItems
-              canViewAuditLog={canViewAuditLog}
-              canViewDeployment={canViewDeployment}
-              canViewAllUsers={canViewAllUsers}
-              canViewHealth={canViewHealth}
-            />
+            <NavItems />
           </div>
         </Drawer>
 
@@ -174,18 +135,20 @@ export const NavbarView: FC<NavbarViewProps> = ({
           )}
         </NavLink>
 
-        <NavItems
-          css={styles.desktopNavItems}
-          canViewAuditLog={canViewAuditLog}
-          canViewDeployment={canViewDeployment}
-          canViewAllUsers={canViewAllUsers}
-          canViewHealth={canViewHealth}
-        />
+        <NavItems css={styles.desktopNavItems} />
 
         <div css={styles.navMenus}>
           {proxyContextValue && (
             <ProxyMenu proxyContextValue={proxyContextValue} />
           )}
+
+          <DeploymentDropdown
+            canViewAuditLog={canViewAuditLog}
+            canViewDeployment={canViewDeployment}
+            canViewAllUsers={canViewAllUsers}
+            canViewHealth={canViewHealth}
+          />
+
           {user && (
             <UserDropdown
               user={user}
@@ -260,7 +223,6 @@ const ProxyMenu: FC<ProxyMenuProps> = ({ proxyContextValue }) => {
         size="small"
         endIcon={<KeyboardArrowDownOutlined />}
         css={{
-          borderRadius: "999px",
           "& .MuiSvgIcon-root": { fontSize: 14 },
         }}
       >
diff --git a/site/src/modules/dashboard/Navbar/UserDropdown/UserDropdownContent.tsx b/site/src/modules/dashboard/Navbar/UserDropdown/UserDropdownContent.tsx
index 631b673b15c0e..c0ad5111ea9ae 100644
--- a/site/src/modules/dashboard/Navbar/UserDropdown/UserDropdownContent.tsx
+++ b/site/src/modules/dashboard/Navbar/UserDropdown/UserDropdownContent.tsx
@@ -27,61 +27,6 @@ export const Language = {
   copyrightText: `\u00a9 ${new Date().getFullYear()} Coder Technologies, Inc.`,
 };
 
-const styles = {
-  info: (theme) => [
-    theme.typography.body2 as CSSObject,
-    {
-      padding: 20,
-    },
-  ],
-  userName: {
-    fontWeight: 600,
-  },
-  userEmail: (theme) => ({
-    color: theme.palette.text.secondary,
-    width: "100%",
-    textOverflow: "ellipsis",
-    overflow: "hidden",
-  }),
-  link: {
-    textDecoration: "none",
-    color: "inherit",
-  },
-  menuItem: (theme) => css`
-    gap: 20px;
-    padding: 8px 20px;
-
-    &:hover {
-      background-color: ${theme.palette.action.hover};
-      transition: background-color 0.3s ease;
-    }
-  `,
-  menuItemIcon: (theme) => ({
-    color: theme.palette.text.secondary,
-    width: 20,
-    height: 20,
-  }),
-  menuItemText: {
-    fontSize: 14,
-  },
-  footerText: (theme) => css`
-    font-size: 12px;
-    text-decoration: none;
-    color: ${theme.palette.text.secondary};
-    display: flex;
-    align-items: center;
-    gap: 4px;
-
-    & svg {
-      width: 12px;
-      height: 12px;
-    }
-  `,
-  buildInfo: (theme) => ({
-    color: theme.palette.text.primary,
-  }),
-} satisfies Record<string, Interpolation<Theme>>;
-
 export interface UserDropdownContentProps {
   user: TypesGen.User;
   organizations?: TypesGen.Organization[];
@@ -268,3 +213,58 @@ const includeBuildInfo = (
     )}`,
   );
 };
+
+const styles = {
+  info: (theme) => [
+    theme.typography.body2 as CSSObject,
+    {
+      padding: 20,
+    },
+  ],
+  userName: {
+    fontWeight: 600,
+  },
+  userEmail: (theme) => ({
+    color: theme.palette.text.secondary,
+    width: "100%",
+    textOverflow: "ellipsis",
+    overflow: "hidden",
+  }),
+  link: {
+    textDecoration: "none",
+    color: "inherit",
+  },
+  menuItem: (theme) => css`
+    gap: 20px;
+    padding: 8px 20px;
+
+    &:hover {
+      background-color: ${theme.palette.action.hover};
+      transition: background-color 0.3s ease;
+    }
+  `,
+  menuItemIcon: (theme) => ({
+    color: theme.palette.text.secondary,
+    width: 20,
+    height: 20,
+  }),
+  menuItemText: {
+    fontSize: 14,
+  },
+  footerText: (theme) => css`
+    font-size: 12px;
+    text-decoration: none;
+    color: ${theme.palette.text.secondary};
+    display: flex;
+    align-items: center;
+    gap: 4px;
+
+    & svg {
+      width: 12px;
+      height: 12px;
+    }
+  `,
+  buildInfo: (theme) => ({
+    color: theme.palette.text.primary,
+  }),
+} satisfies Record<string, Interpolation<Theme>>;
diff --git a/site/src/modules/navigation.ts b/site/src/modules/navigation.ts
new file mode 100644
index 0000000000000..74217a4ceaaac
--- /dev/null
+++ b/site/src/modules/navigation.ts
@@ -0,0 +1,7 @@
+/**
+ * @fileoverview TODO: centralize navigation code here! URL constants, URL formatting, all of it
+ */
+
+export const USERS_LINK = `/users?filter=${encodeURIComponent(
+  "status:active",
+)}`;
diff --git a/site/src/pages/UsersPage/UsersLayout.tsx b/site/src/pages/UsersPage/UsersLayout.tsx
index bb85cae1b03b8..8b3dc7858c41e 100644
--- a/site/src/pages/UsersPage/UsersLayout.tsx
+++ b/site/src/pages/UsersPage/UsersLayout.tsx
@@ -13,8 +13,8 @@ import { Margins } from "components/Margins/Margins";
 import { PageHeader, PageHeaderTitle } from "components/PageHeader/PageHeader";
 import { TAB_PADDING_Y, TabLink, Tabs, TabsList } from "components/Tabs/Tabs";
 import { useAuthenticated } from "contexts/auth/RequireAuth";
-import { USERS_LINK } from "modules/dashboard/Navbar/NavbarView";
 import { useFeatureVisibility } from "modules/dashboard/useFeatureVisibility";
+import { USERS_LINK } from "modules/navigation";
 
 export const UsersLayout: FC = () => {
   const { permissions } = useAuthenticated();